


Pulling Pigtails (it's more about lifting skirts)

by mensuramjr



Category: Teen Wolf (TV)
Genre: Bottom Stiles Stilinski, Comeplay, Crossdressing, Crossdressing Stiles Stilinski, Derek is a Failwolf, Dom Derek, Drag Queens, First Kiss, First Time, Gay Bar, Humiliation, Humor, Illustrated, Illustrations, Light Dom/sub, Light Sadism, Lydia Martin & Stiles Stilinski Friendship, M/M, Oblivious Stiles, Other Additional Tags to Be Added, Pack Mother Stiles Stilinski, Panties, Panty Kink, Romantic Comedy, Self-Acceptance, Sexual Identity, Sub Stiles, Top Derek Hale, Virgin Stiles, all the humiliation, because derek, but also kinda not, can't believe there's a tag for that, humiliated stiles, so is Derek, stiles is kind of an idiot, though the Dom/sub thing is kind of a joke
Language: English
Status: In-Progress
Published: 2014-05-21
Updated: 2014-05-23
Packaged: 2018-01-26 00:05:23
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 2
Words: 3,418
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/1667399
Author URL: https://archiveofourown.org/users/mensuramjr/pseuds/mensuramjr
Summary: <blockquote class="userstuff">
              <p>Derek never imagined himself finally getting into the "pulling pigtails and lifting skirts" period of his life at 23. Because damn that kid and his stupid eyes and his stupid name and his stupid everything. Especially those god damned panties. In which there is panties!Stiles, failwolf!Derek and the author never meant to write a rom-com. Canon up til end of s2.<br/>NOW WITH illustrations by me because we all need ACTUAL VISUAL DEMONSTRATION.</p>
            </blockquote>





	1. Chapter 1

**Author's Note:**

> Yeah... So I've finally gotten a few acceptance letters from schools I've wanted in. So my half-year exile ends as my search for the perfect uni ends.
> 
> Anyway, back with a new teen wolf fic, and hope you liked it so far, it's inspired by a manga I read a month ago, though I can't quite remember the name, if you spot the references, COOKIES! But don't worry the similarities will come to an end soon as the personalities are extremely different. (So please don't sue me!)
> 
> I've planned as far as about half, though I've plenty of slots to fit in some suggestions, so prompt me! (Like, Lydia and Stiles become panties!bros or something like that)
> 
> Also, beta anyone?
> 
> Ps, I swear I'll finish my Percy Jackson fic once I remember where I shoved the draft. SORRY.

 

 

 

 

He's not entirely sure why he ends up feeling guilty about what happened to Stiles and his ride, but it's not like he lacks the money, so he ends up sneaking into his room when the little bastard's at school, and decides to at least help him with his jeep's repair. Of course, preferably without Stiles ever knowing.

Derek has no illusions to how much of a dick he is, but more than anything Derek doesn't like unpaid favors, especially those of the life-saving variety, and he is adamant in rectifying said problem. Not that Stiles would think of it that way, which is precisely why he's hoping he could get the repaying part done with Stiles being none the wiser.

Well, he could hope.

So it is when Derek ends up in Stiles' room, that he accidentally comes across... Well. This.

* * *

Stiles was not meant to be home for another hour so Derek was relatively relaxed sneaking in through the window. Cash in hand and... Surprisingly, Stiles' heart beat was there as well. Even more surprising, and was what lead to Derek totally ignoring the quickened heart beat, was a pair of white lace  _panties_  barely held together by salmon pink ribbons on the sides.

He isn't sure what such a flimsy piece of cloth is supposed to achieve. He's quite certain he's never seen anything quite so revealing or lacy... And Derek grew up with two sisters along with an overwhelming amount of cousins. Which includes  _Laura_ , so that's saying something.

Derek could feel his brows rise up - both brows this time; and holding up the tiny panties ( _panties!_ ) between his thumbs and forefingers in morbid fascination, as Stiles came bursting through the door in a panic.

"Oh god, oh  _god_. Where the fuck is it?"

Derek, still too rooted to the spot in mortification to react to the fact that Stiles had actually managed to sneak up on him, to actually respond in a proper surprised fashion. When Stiles finally took in the sight of the werewolf lightly tugging on the scrap of lace between two fingers, testing the elasticity, panic quickly turned into  _panic attack_.

Seeing his horrified expression, Derek felt his brain kick into gear. Honestly if he hadn't been able to scent the lack of female he would have accused Stiles of going  _way_  to far with his Lydia crush. As it is however, before he was able to reprehend (and maybe laugh at) Stiles about lingerie boutique thefts, apparently the horror had finally caught up and managed to break the teen's already malfunctioning filter.

"Okay, first of all, those aren't meant for women, those are men's lingerie."

"Huh?"

So the awkward element to Stiles is in truth slightly amusing to Derek, even if he doesn't ever admit it.

"So what if it looks a little bit unconventional... Fine. A lot unconventional." And it kind of makes him want to laugh at the spastic teen.

"But it is totally a legit thing. Legal.  _Completely_  legal and consensual, also completely unfair prices but still. PayPal." And they really don't get along at all. But the usual flailing and twitching awkwardness, has absolutely nothing on the mortified downtrodden look he has now.

"It's completely normal, sort of. Anyone buys them. Well, anyone can buy them." Which is why Derek feels a bit sorry for him, the pity is almost nonexistent of course. Though the main reason why he stops Stiles' rant is because it's starting to veer away from incredibly hysterical towards extremely annoying.

"Stiles - "

" - Which is why I bought 'em. Like a normalish person should."

"STILES." Stiles lets out a gratifying whimper. "Shut up."

Derek watches as the boy forces down his ramble and instead nervously gnawing at the tassels of his hoodie.

"I have no idea what - nor do I want to know -" he says, and decides to cut the boy some slack, "but whatever is going on up there, stop it. I'm not gonna tell anyone so just relax."

"Derek -" he could just see the hopeful little sparks twinkling in his eyes, and irritatingly, a pang of uncharacteristic sympathy wells up inside his cold, absolutely withered and unfeeling heart.

He sighs.

"This is obviously just a personal... Hobby of yours, there's nothing wrong with a bit of self-indulgence." He swallows, "even I have some... Fangy tendencies." He manages to confess his fantasies about wolfing-out when having sex while maintaining a straight face, and feels extremely accomplished with how red Stiles is getting in comparison. He is also slightly relieved he got to confess said fantasy while Stiles is still obviously out of his depth and hopefully won't get to the more awkward questions.

With a cough he continues, "what other cuts do you have?" He desperately wants to disrupt the mental melt-down, so... A little encouragement goes a long way, at least according to Laura.

"It's not fading at all despite the worn scent it holds. I can tell you've been treating it with care and hand washing them." Derek tries to smile in what he hopes is a reassuring manner, it feels more like a grimace but apparently it's working because Stiles looks as if Derek just bought him a PS4 and is on the verge of emotion filled tears.

Derek really just wanted work on a little compassion once in a while, and the money in his pocket seem fleeting and cheap when compared to the obvious gratitude and warmth in Stiles' eyes.

"Would... Would you like to see?" Stiles looks up through his lashes as he shyly offers.

"WHAT."

Which is how Derek knows Laura is wrong, and Stiles is completely right about his emotional constipation, and he should have  _never_  attempted to rectify that.

At least Laura's incapable of laughing at him now.

 

* * *

 

The panties Derek finds, done by moi, and how does one Stiles-moles? ->

updated 5/22


	2. Chapter 2

**Summary for the Chapter:**

> Stiles enthusiastically shows Derek his collection, and it's hell on earth for the werewolf. Until it's not.

**Notes for the Chapter:**

> well that was fast, may I remind everyone there are gonna be illustrations on the ao3 ver. (Link on my profile) and that there will be a vote for this chapters pic at the end of this chapter as well. ^^
> 
> warnings: sort of dub-con(more info at the end of chapter, read if you need to.), inappropriate humor, and foul language.
> 
> enjoy!

After a great bout of regret and self-reprimand, Derek was promptly sat at the desk, pinching the bridge of his nose as he watched Stiles crawl under the bed (the hiding place tragically unsurprising) with his ass waving in the air. Stiles dragged a sleeping bag out, laughing nervously as he unzips it.

Under Derek's reluctant curiosity, the sleeping bag reveals... blankets. Stiles coughs as he says, "just in case, ya' know." The sheets and blankets are pulled aside to reveal a suitcase.

Before Derek could get too impressed however, Stiles unlocks the suitcase with - predictably - his birth date. He rolls his eyes and Stiles blushes, "whatever dude, it's not like anyone's gonna actually  _find_  this anyway, it's just to make me feel better... Which... how exactly did you know that was my birthday?"

Derek ignores him, also failing to remind Stiles that the only ones who  _could_  stumble upon the suitcase are the ones who would guess the password.

Stiles opens the lid.

* * *

Stiles... Stiles is practically a collector, there are rows upon rows of neat little squares holding the panties (holy  _shit_  that is a lot of panties.) Derek vaguely registers there is some sort of categorizing system going on, and Derek isn't sure if he wants to understand how a boy sorts his lingerie, because lingerie is the only word for this.

Derek thinks Stiles could start his own boutique.

He also thinks he's finally figured out why Stiles doesn't lead a more extravagant life style; Stiles' no Jackson or Lydia, but the occupation of sheriff must at least pay better than a nurse, which makes Scott and Stiles' similar quality of life seem just a  _little_  suspicious... "Is this why you still drive that piece of... Your jeep. I don't even know how much you pay for just  _one_  of these..."

Stiles looks just a little offended at that. "Don't be such a jerk. Carrie was my Mom's, and my Gran's before that." Derek feels a bit sheepish at that, and simply asks, "Carrie?"

"You know, like carry your stuff around but it's also a name? Gran bought it as her own 50 year-old birthday present, but gave it to us when my mom had me... Why am I telling you this?" It was actually a pretty nice story, but more than anything Derek just wanted to groan. "Seeing as your grandmother named it I'm guessing the sense of humor runs in the family."

"Whatever," he blushed. "I'll have you know even they consider me the funniest."

Derek really doesn't want to linger on the mental image of more than one Stiles, so he goes for a distraction tactic. "Did you actually make those compartments yourself?"

Stiles Beams.

* * *

It's been 2 hours.

Derek suspects he's accidentally prodded some deeply closeted desires Stiles had been keeping at bay for who knows how long, and he's hanging onto this never before chance to wax poetic about his undergarments for dear life. But Derek has learnt  _way_  too much about -

"-and those ones you saw earlier really has cotton lining, I mean, I do adore it, and it's loads better than polyester, but I really,  _really_ prefer pure lace or satin. Like the ones in the top column -"

Derek began zoning out around the half-hour mark, but apparently Stiles is still blubbering on about material. Jesus, he could hardly fathom talking about underwear  _in general_  for an hour. If he wasn't suffering through this now he would  _never_  believe one could go on about just  _one_  aspect of lingerie for over 2 hours without ever slowing down.

"-Though the thing about satin is you have to be really careful and hand wash them, and you can't even wring them out. Also you have to iron them, which is awkward because Dad keeps the iron in his room for his uniform- "

* * *

Derek feels his amazement grow as another hour passes.

It's not that Derek doesn't understand nice underwear, he does, Derek owns four pairs of nice, comfortable, and immensely satisfactory CK boxer briefs, Laura got them. (There was a talk about no brother of hers were allowed to wear tighty-whities involved, but Derek doesn't think about that.)

Somewhere along the way he noted there were two levels in Stiles' "treasure chest", so Derek is terrified and praying to the moon and whatever gods there are to not have Stiles "share" that, too.

He was in the middle of testing the elasticity of a Spandex thong Stiles offered him to display "what real good quality elastine is supposed to mean", that Derek finally, truly comes back to his senses, and asks with a croak, "What in the world is wrong with  _boxers_?!"

It's the wrong thing to say.

Stiles had the audacity to look scandalized, and said with eyes wide, "But... but it's so...  _baggy_ , and  _loose_  and... and don't you get cold? I mean boxer briefs are fine I guess, but like this part here-" he's holding a more traditional and worn pair of boxers appallingly, Derek thinks those must be what he wore before he "saw the light".

He's grimacing as he points at various sections at the trunks and waist. "- or the waist, is  _completely_  unnecessary. Especially the waist line, nothing should go above hip height, ever - unless it's a string cut, but  _only_  if it's high on the side, the center piece should  _always_  stay at hip level, period. I also don't get how people stand the thigh length trunks..."

Derek just nods along dumbly.

"Speaking of which Derek, do you actually wear those... things with the  _buttons_  and  _pouches_? No offense of course." Derek thinks he should feel offended on behalf of those who do anyway.

"No... " Who gives a flying fuck? How the fuck does it matter? The only function of underwear is to stop your god damn dick from chafing against your fucking jeans. That's it.

"SEE? I knew I was right. But anyway my collection just kinda grew after the internet." Stiles was stroking at the case fondly as he continues, "And there were just so many to choose from, cute pieces and some I find rather dashing... I really just wanted some quality bikini briefs at first but then..." Derek doesn't know if finding this new side to the migraine inducing teen is a blessing or a curse.

"You're right you know, I can't stop myself from getting more, I still haven't managed to save up for a PS3 because of this, I always end up blowing it over the next set of tie-side briefs or something. Honestly I don't know what to do with myself either."

"I mean, I sometimes think my thing for Lydia is really because I know I'm never gonna be able share this with a girlfriend, so I might as well pine after a girl I'll never have, you know what I mean?" Stiles looks at him with the barest hint of vulnerability. "You know, I'm glad it's you who found my panties and not my Dad or god forbid Scott. Because, Scott. It's nice being able to talk about this to someone. So. Thanks."

Derek looks at the bashful expression and... really just feels a bit baffled. "You're kind of an idiot, you could have just said it was your girlfriend's."

"But... Everyone knows I've never had one before." Stiles continues a bit uncomfortably, "and you would have been able to smell it if it were a girl's"

"Exactly, which would have meant you stole them, and that's still better than confessing a crossdressing fetish to the werewolf who almost made you cut off his arm."

Stiles let out a slightly hysterical laugh. "Yeah. Yeah you're right. I just panicked and broke my brain. I guess I didn't know what to do except getting all defensive. But... you're not so bad Derek. Really."

"The surprised tone, though expected, is still insulting." Derek deadpanned, he isn't sure if Stiles can tell he's amused.

"Like you don't spend your time shoving me into walls and threatening me with bodily harm every time something supernatural bites us in the ass."

"Don't get too cheeky, I might just tell the whole pack next time there's a meeting."

"For some reason I actually don't think you're gonna do that."

Derek actually does feel insulted this time. He growls to make a point.

"Not to undermine your Alpha authority of course, I'm still terrified you're gonna disembowel me in private. I just don't think you'll tell everyone. You're still fucking scary. Just...  _Put the teeth back please_." The fear scent properly mollifies Derek, and he retracts his fangs, and walks to the window.

"You have school tomorrow yeah? Go to bed. I think I've had enough of panties." Derek opens the window, then pauses. "Speaking of school, you actually wear that to school?"

"Of course not!" Stiles squeaks. He's already put everything back in the sleeping bag and shoving it under the bed. "I only wear them after I come home and usually after my bath."

"That makes sense, I was wondering about the locker rooms." Derek takes a look at the sweatpants and worn hoodie Stiles, and notes the smell of soap. "Which means... You're wearing a pair  _right now_."

"Huh?... Wha... Yeah, so?... Derek?" Derek felt an inexplicable urge rise within."Derek. Do I want to know what that face means?  _Derek_?"

Derek grunts as he looks down at Stiles' crotch, it doesn't look  _nearly_  as big as his, but still... "Let me see your panties."

" _What_."

"Let me see what kind you're wearing right now." Derek crowded forward.

"Wait, what the fuck are you talking about? Are you high? Wait no, werewolves. Did you inhale some of my mountain ash? Do I have to call Deaton?" Stiles has never looked quite so terrified as he shuffled away from the stalking Alpha.

They were almost back at the desk when Derek started getting handsy and grabbed at Stiles.

"What does it matter, I've already seen your collection." Stiles was trying his best to break out of the grapple as he shouted back, " _are you out if your mind?!_ "

"It's really getting to me. I  _have_ to know what exactly happens to such a small piece of fabric," he stubbornly pressed on.

"That... That doesn't even make sense!" Stiles incredulously spat after the command made him freeze in place, which made him trip against the chair and both human and were went tumbling to the ground. Stiles shrieked.

"Sorry." Derek stated as Stiles hit the floor with the Alpha atop him.

"What kind of half-assed apology is  _that_? I can almost  _taste_  the mockery," Stiles squeaked. Derek gave a wolfish grin.

"Stop being such a baby. It's not gonna kill you." Derek moved to cover Stiles.

"Stop... Stop being such a..." Stiles stuttered with disbelief, then sensing Derek's movement, quickly scrambled to his hands and knees to crawl away. "Derek,  _do you even hear yourself?!_ "

"Shut up and let me see your panties." However quick Stiles made his escape, Derek was a werewolf, and had no qualms about abusing his powers. So it was like taking candy from a baby when he grabbed onto the slim waist before him.

"WAIT, NO. BAD DOG... BAD TOUCH! STOP!" Stiles was struggling with all his might, but Derek was the Alpha, and he was determined.

"NO! NOT TODAY'S!" Derek could feel an unhealthy amount of satisfaction as he watched Stiles began to flush pink, and the air grow thick with the scent of humiliation, panic, and interestingly though faint, arousal. It was one thing to see panties objectively, and acknowledge a boy wears them, but another entirely to actually  _see_  them on Stiles.

Somehow the prospect of seeing them in person, drove Derek to a singleminded determination. Derek knows he's probably giving his wolf way too much control, but seeing as they aren't exactly separate identities, he thinks he should probably do some thorough self-analyzing.

After he  _rips_  these god damn pants  _off_ , of course.

Derek finally succeeded in shoving his fingers into the waistband of Stiles' sweatpants as he reached the door and had no where left to turn. Derek smirked in satisfaction as his fingers brushed lace, Derek tightened his grasp, and  _tugged_.

The gray fabric of the sweatpants easily slipped past the pert globes beneath him, conveniently binding Stiles' knees and calves to immobility. Derek vaguely registered a strangled whimper, but only just, because this... This was  _not_  what he had in mind.

Derek pictured awkward bulges and rigid bones, but what was actually in front of his eyes was decidedly not awkward. In fact, Derek's pretty sure the image was now permanently burned into his retinas.

The pale mole dotted skin across a thin frame was the only part Derek could have anticipated. The shapely hips and suggestion of lightly toned legs were a complete surprise, but what was most shocking, was the pathetic excuse for fabric stretched tightly across the perkiest ass he's ever seen.

In a sense there was actually  _more_  material than the set Derek first stumbled across. But while that set had lace trim, these were  _completely_  made of lace, making it incredibly... Revealing. Through the intricate weave of black thread, Derek could glimpse the full mounds and tantalizing crease teasing him through the floral patterns of delicate embroidery. He swallowed thickly.

"Is that... Is that as transparent as I think it is?" Much like Derek, Stiles was frozen to the spot in shock. "I don't think I've ever seen anything even close to that outside of some explicit French art film."

"I told you not today. I fucking  _told_  you," he wailed, his voice on the verge of tears. "I knew I shouldn't have shown you all that."

Still mesmerized, Derek tugged on the waistband. Stiles slapped his hand off. "Jesus,  _stop that_."

Stiles jumped to sit up, pushing down the hem of his hoodie and curling his legs up to cover the front as he sat back against the bedroom door.

"So... So humiliating... Fuck you Derek." Derek could see his face now, Stiles wasn't actively sobbing or anything, but he was shivering and scarlet all over. Derek couldn't deny the bright, misty amber eyes were disgustingly appealing, nor the fact that the red rim and dewy lashes made his wolf howl in sadistic glee. "Could you please,  _please_  stop toying with the human?"

"I... I wasn't toying with you," Derek confessed with honesty that surprised even himself. Stiles just sniffled and gnawed at his trembling lower lip as he perplexedly stared back. Derek's heart pounded.

"To be honest... It's... Rather intriguing?"

" _WHAT_?"

**Notes for the Chapter:**

> So, warnings, don't read beyond the this paragraph if you're afraid of further spoilers:
> 
> Dub-con but not in the rapey sense but in the forced stripping sense, and really it's just improper humor, Stiles is more mortified than actually getting all angsty and violated. I don't say non-con because Derek tbh, isn't really all himself in a sense, and he could sense Stiles getting turned on. Of course no means no and even if there are two boners don't make bad touch okay, but... It's a comedy and even torture can be funny in comedy okay? (At least for me)
> 
> okay, warning over.
> 
> So I'm still looking for a beta. And damn that was a lot of foul language and damn that was the longest chapter (2.8k) I've ever written. don't worry there'll be an illustration for this chapter as well, you kinky bastards. ;)
> 
> VOTE TIME: (on my profile on fanfiction dot net, and in comments in Ao3)
> 
> would you rather I-
> 
> a) include some more serious(okay not that serious) stuff like bad guy ass kicking and supernatural shit going on, maybe add mate fic aspects? or-
> 
> b) nah lets just get it on with all the smut and panty kink.
> 
> I'm not gonna cut down on the smex if you choose, just there will be more plot and will take longer for me to write if this gets beyond PWP since I have to, you know, scheme. Basically, Porn with or without plot?
> 
> vote ends at Monday. BYE.

**Author's Note:**

> PS: The illustrations are always up one to two days after the chapter, feel free to put in suggestions! Or if there's a particular panty/thong/dress/skirt/whatever you'd like to see, comments!


End file.
